Play the Full 90: A Mid-Year Tax Game Plan for Entrepreneurs

The World Cup is at halftime. Is your business tax strategy?

The 2026 FIFA World Cup is happening right now across the United States, Canada, and Mexico — 48 teams, 104 matches, and millions of fans watching every move. While the world focuses on penalty kicks and golden goals, smart entrepreneurs know that mid-July is also one of the most important moments in the financial year.

Just like a soccer team that coasts through the first half only to panic in the second, business owners who ignore taxes until April are already playing from behind. The good news? Halftime adjustments work in business too, if you make them now.

Here’s your mid-year tax game plan.

Know Your Formation: Are You in the Right Business Structure?

Every great team starts with the right formation. Run the wrong one and even talented players get exposed.

The same is true for your business entity. The structure you choose affects self-employment tax, payroll tax, liability protection, and how much flexibility you have as profits grow.

It may be worth reviewing whether your current structure, such as a sole proprietorship, corporation, LLC, or S corporation, is still the right fit. The right entity can affect self-employment taxes, payroll requirements, liability protection, and overall tax savings.

Make Your Substitutions: Mid-Year Tax Moves That Still Count

In soccer, substitutions made at the right moment can change the outcome of a game. The same is true in tax planning, but the window closes faster than most business owners realize.

Now is the time to check whether your estimated tax payments are on track. If revenue has increased this year, you may need to adjust upcoming payments to avoid penalties.

It’s also a good opportunity to:

• Review retirement contribution opportunities
• Review home office deductions if you qualify
• Consider whether you should be investing in any capital improvements that can be fully depreciated
• Plan for the qualified business income deduction
• Review charitable giving
• Plan for material year end expenditures to help reduce income

Avoid the Red Card: IRS Audit Triggers for Entrepreneurs

A red card can change a match instantly. An IRS audit or tax notice can have meaningful impacts to your business. They can limit cash and consume time and energy you would rather spend growing the company.

Here are some of the fouls that may attract attention:

• Large deductions out of line with your income or industry
• Worker misclassification – independent contractor vs. W-2 employee
• No officer wages (if classified as an S corporation)
• Schedule C repeated business losses (hobby-loss risk)
• Foreign accounts and unreported foreign income
• Consistently changing accounting methods

The New Rules of the Game: Important OBBBA Changes

2025 brought major rule changes to the tax field through the One Big Beautiful Bill Act. The OBBBA restructured the tax landscape across four major areas: individual tax provisions, business tax provisions, energy tax credits, and health-related tax changes.

These changes should certainly be factored into your 2026 tax planning.

For more information on these changes, check out the following articles:

How the One Big Beautiful Bill Act Will Affect Your Individual Taxes – https://www.muacllp.com/insight/how-the-one-big-beautiful-bill-act-will-affect-your-individual-taxes/

How the One Big Beautiful Bill Act Will Affect Your Business Taxes – https://www.muacllp.com/insight/how-the-one-big-beautiful-bill-act-will-affect-your-business-taxes/

Manage the Clock: Key Deadlines Before Year-End

Great teams do not just play well, they manage the clock. Here are the dates that you should be aware of:

July 31, 2026:

• Q2 payroll tax return due (Form 941, for most employers)

September 15, 2026 :

• Q3 estimated tax payments due;
• Extended deadline for 2025 S-corporation and partnership returns

October 15, 2026

• Extended deadline for 2025 individual returns and C corporation returns

December 31, 2026

• Last day to pay many deductible 2026 business expenses if you are a cash-basis taxpayer

January 15, 2027

• Q4 estimated tax payments are due

Champions Plan Ahead

The teams that win the World Cup do not figure out strategy in the 89th minute. They enter every match with a plan, make smart adjustments at halftime, and execute with discipline.

Your business deserves the same approach.

Mid-year is the perfect time to sit down with your accounting team, review what is working, catch problems before they become penalties, and make sure you are using every deduction and strategy available.

Ready for a Mid-Year Tax Checkup?

Our Entrepreneurial Services team works with business owners to develop proactive tax strategies that support long-term growth. If you’d like to review your tax position, evaluate your entity structure, or identify planning opportunities before year-end, we’d be happy to help.